Exploring Regioselective Bond Cleavage and Cross-Coupling Reactions using a Low-Valent Nickel Complex

2016 ◽  
Vol 22 (12) ◽  
pp. 4070-4077 ◽  
Author(s):  
Addison N. Desnoyer ◽  
Florian W. Friese ◽  
Weiling Chiu ◽  
Marcus W. Drover ◽  
Brian O. Patrick ◽  
...  
Keyword(s):  
Nickel Complex ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Low Valent

Ni(COD)(DMFU): A Heteroleptic 16-Electron Precatalyst for 1,2-Diarylation of Alkenes

Synlett ◽  
2021 ◽  
Author(s):  
Nana Kim ◽  
Van T. Tran ◽  
Omar Apolinar ◽  
Steven Wisniewski ◽  
Martin Eastgate ◽  
...  
Keyword(s):  
Nickel Complex ◽  
Active Catalyst ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Beneficial Effects ◽  
Cross Coupling Reactions ◽  
Growing Body ◽  
Hydride Elimination

Electron-deficient olefin (EDO) ligands are known to promote a variety of nickel-catalyzed cross-coupling reactions, presumably by accelerating the reductive elimination step and preventing undesired β-hydride elimination. While there is a growing body of experimental and computational evidence elucidating the beneficial effects of EDO ligands, significant gaps remain in our understanding of the underlying coordination chemistry of the Ni–EDO species involved. In particular, most procedures rely on in situ assembly of the active catalyst, and there is a paucity of pre-ligated Ni-EDO precatalysts. Herein, we investigate the 16-electron, heteroleptic nickel complex, Ni(COD)(DMFU), and examine the performance of this complex as a precatalyst in 1,2-diarylation of alkenes.

scholarly journals Well-Defined Pre-Catalysts in Amide and Ester Bond Activation

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 215 ◽  
Author(s):  
Sandeep R. Vemula ◽  
Michael R. Chhoun ◽  
Gregory R. Cook
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Ester Bond ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Design And Synthesis ◽  
Cross Coupling Reactions ◽  
Made In

Over the past few decades, transition metal catalysis has witnessed a rapid and extensive development. The discovery and development of cross-coupling reactions is considered to be one of the most important advancements in the field of organic synthesis. The design and synthesis of well-defined and bench-stable transition metal pre-catalysts provide a significant improvement over the current catalytic systems in cross-coupling reactions, avoiding excess use of expensive ligands and harsh conditions for the synthesis of pharmaceuticals, agrochemicals and materials. Among various well-defined pre-catalysts, the use of Pd(II)-NHC, particularly, provided new avenues to expand the scope of cross-coupling reactions incorporating unreactive electrophiles, such as amides and esters. The strong σ-donation and tunable steric bulk of NHC ligands in Pd-NHC complexes facilitate oxidative addition and reductive elimination steps enabling the cross-coupling of broad range of amides and esters using facile conditions contrary to the arduous conditions employed under traditional catalytic conditions. Owing to the favorable catalytic activity of Pd-NHC catalysts, a tremendous progress was made in their utilization for cross-coupling reactions via selective acyl C–X (X=N, O) bond cleavage. This review highlights the recent advances made in the utilization of well-defined pre-catalysts for C–C and C–N bond forming reactions via selective amide and ester bond cleavage.

Cross coupling reactions of multiple CCl bonds of polychlorinated solvents with Grignard reagent using a pincer nickel complex

2012 ◽  
Vol 363-364 ◽  
pp. 322-327 ◽  
Author(s):  
Yashraj Gartia ◽  
Abhijit Biswas ◽  
Matthew Stadler ◽  
Udaya Bhasker Nasini ◽  
Anindya Ghosh
Keyword(s):  
Grignard Reagent ◽  
Nickel Complex ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Palladium catalyzed Suzuki cross-coupling of benzyltrimethylammonium salts via C–N bond cleavage

RSC Advances ◽  
2017 ◽  
Vol 7 (26) ◽  
pp. 15805-15808 ◽  
Author(s):  
Tao Wang ◽  
Shuwu Yang ◽  
Silin Xu ◽  
Chunyu Han ◽  
Ge Guo ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Efficient Approach ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Way

A Pd catalyzed Suzuki cross-coupling of a benzyltrimethylammonium salt is described. This reaction offers a highly efficient approach to diarylmethanes and also paves the way for the application of benzyltrimethylammonium salts in Pd catalyzed cross-coupling reactions.

scholarly journals Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

2020 ◽  
Author(s):  
Megan Greaves ◽  
Thomas O. Ronson ◽  
Guy Lloyd-Jones ◽  
Feliu Maseras ◽  
Stephen Sproules ◽  
...  
Keyword(s):  
Alkyl Radical ◽  
Nickel Complex ◽  
Cross Coupling ◽  
Active Species ◽  
Alkyl Halides ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Alternative Pathways ◽  
Cross Coupling Reactions ◽  
Abstraction Reaction

The mechanism of the reactions between dppf-Ni0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(dppf)2], which undergoes a halide abstraction reaction with alkyl halides and rapidly captures the alkyl radical that is formed. The yields in prototypical nickel-catalysed Kumada cross-coupling reactions are shown to be improved by the addition of free phosphine ligands<br>

Polycrystalline boron-doped diamond electrodes for electrocatalytic and electrosynthetic applications

2017 ◽  
Vol 53 (8) ◽  
pp. 1338-1347 ◽  
Author(s):  
Tribidasari A. Ivandini ◽  
Yasuaki Einaga
Keyword(s):  
Bond Cleavage ◽  
Cross Coupling ◽  
Diamond Surface ◽  
Coupling Reactions ◽  
Diamond Electrodes ◽  
Boron Doped Diamond ◽  
Cross Coupling Reactions ◽  
Boron Doped

When oxyl groups react with a conducting diamond surface, the formed oxyl spin centers can induce alkoxylation, bond cleavage, coupling and cross-coupling reactions.

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